Henry was born on July 23, 1863 in Newport, Kentucky to Herman Eilerman & Maria Borg. Per Henry's Obituary posted in the Lima Morning Star, January 26, 1931, Henry also went by the name "Bob".

On June 22, 1898, Henry married Anna Mary Ridder, he was 34 years old and she was 19 years old. They had one child together: (1) Robert Herman Eilerman. Less than a week after giving birth, Anna Mary passed away due to complications from the birth.

On October 24, 1900, Henry married Elizabeth Clara Ridder in Newport, Kentucky, he was 37 years old and she was 16 years old. Elizabeth was younger sister to Henry's 1st wife, Anna Mary. When Anna Mary passed away, Elizabeth took care of their child, Robert. Shortly after, she and Henry married. In the span of 20 years, Henry and Elizabeth had at least 10 children together: (1) Marie Elizabeth Eilerman; (2) Romaine Cecelia Marie Eilerman; (3) Albert George Eilerman; (4) Louis John Eilerman; (5) Leo August Eilerman; (6) Leonard Bernard Eilerman; (7) Henry Andrew Eilerman; (8) Rita Florence Eilerman; (9) Dorothy Rose Eilerman; (10) Elizabeth Ann Eilerman. Therefore, Henry's 1st child was both a half-sibling and cousin to his other 10 children.

Henry worked for his father (along with his brothers) at Eilerman & Sons in Kentucky; they sold men's fine clothing and hats. In 1901 Henry, relocated to Lima, Ohio and opened up his own Eilerman's clothing store. Henry's business was successful and survived for 30 years, even through the Great Depression, but closed shortly after his death. His wife Elizabeth received everything but the store was liquidated shortly after Henry's passing.

On July 23, 1863, Henry passed away from Uremia (kidney issues) at the age of 67 years old in Lima, Ohio.